Novel copolymers of styrene. 7. Some ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates |
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Authors: | Gregory B Kharas Valeria A Sloan-Lyon Monika Cieszynski John D A Manuel Steve L Mei John B Mubang Jr |
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Institution: | 1. Chemistry Department, DePaul University, Chicago, ILgkharas@depaul.edu;3. Chemistry Department, DePaul University, Chicago, IL |
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Abstract: | Novel trisubstituted ethylenes, ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH = C(CN)CO2C3H7 (where R is 2-bromo-5-methoxy, 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-chloro-3-methoxy, 3-chloro-4-methoxy, 2-fluoro-3-methoxy, 2-fluoro-4-methoxy, 3-fluoro-4-methyl, 4-fluoro-3-phenoxy) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the ethylenes were copolymerized with styrene (M1) in solution with radical initiation (ABCN) at 70°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR, GPC, DSC, and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500°C range with residue (3–7% wt.), which then decomposed in the 500–800°C range. |
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Keywords: | Trisubstituted ethylenes radical copolymerization styrene copolymers |
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